Synthesis of a Chiral Auxiliary Family from Levoglucosenone and Evaluation in the Diels–Alder Reaction
Keyword(s):
A new family of chiral auxiliaries has been developed based on the lignocellulosic biomass pyrolysis product levoglucosenone. A promising single stereoisomer with an alcohol and π-stacking phenyl substituents was prepared in excellent yield in two steps from dihydrolevoglucosenone without chromatography on >50 g scale. Acrylate esters prepared from the auxiliaries underwent diastereoselective Lewis acid promoted Diels–Alder reactions with cyclopentadiene (endo/exo 98:2, endo d.r. up to 98:2), dimethylbutadiene (d.r. 93:7), and isoprene (d.r. > 98:2)
2009 ◽
Vol 50
(9)
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pp. 999-1002
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2003 ◽
Vol 44
(3)
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pp. 431-433
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1990 ◽
pp. 426-428
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1999 ◽
Vol 10
(24)
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pp. 4831-4840
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2003 ◽
Vol 68
(25)
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pp. 9809-9812
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